Sulfuric Acid → (1S,2R)-Indene oxide

HRID 265740Notes

Reaction equation

Br[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1Br.S(=O)(=O)(O)[OH:13]>C(#N)C>[O:13]1[C@@H:3]2[CH2:4][C:5]3[C:10]([C@H:2]12)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

Conditions

Temperature: 40 °C

Procedure

Into a 1000 ml four-neck flask, 259.5 g of an acetonitrile solution of 1,2-dibromoindan (corresponding to bromination of 0.559 mol of indene) was introduced. It was then heated to 40° C. To this solution, 86.57 g (0.839 mol) of 97% sulfuric acid was dropwise added at 40°-46° C. in a period of 1.5 hours. The resulting mixture was stirred at the same temperature for 5 hours. According to an HPLC analysis, about 15% of 1,2-dibromoindan was remaining in the mixture. To this mixture, 43.29 g of sulfuric acid was further added. The resulting mixture was stirred at 50°-60° C. for 1.5 hours. According to an HPLC analysis, 1,2-dibromoindan had almost disappeared yielding 11.0% of trans-amide derivative (III: R=CH3) and 25.3% of cis-oxazoline derivative (IV: R=CH3).

Workup

stirringThe resulting mixture was stirred at 50°-60° C. for 1.5 hours

Sources & evidence

ORD record: ord-0d458213e3aa4d6c879f41039387077c
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648534

Reaction notes

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